1. A quilted jacket set that takes the guesswork out of layering. Plus, the neutral colors make it easy to mix and match with your little one's other fall staples.

Carter's

Price: $35 (originally $46; available in sizes 2T-5T)

2. A striped Henley top so your toddler can get in on the rugby shirt trend.

Carter's

Price: $18 (available in two colors)

3. A pair of high tops that can transition from the playground to school to nicer events, where your toddler still needs comfortable footwear to show off their moves.

Carter's

Price: $32 (originally $42; available in two colors and in sizes 4-12)

4. A jumper dress set for aesthetic pumpkin patch photo shoots or just a day at the park.

Carter's

Price: $22.80 (originally $38; available in sizes 2T-5T)

5. A quilted jacket that adds to the outfit instead of just covering it up. The scalloped pockets! The floral interior!

Carter's

Price: $26 (originally $42; available in sizes 2T–5T)

6. A varsity outfit set for your budding sports star. Wear the matching set for a full game day celebration, or one piece at a time for a more subtle athletic look.

Carter's

Price: $35 (originally $46; available in sizes 2T–5T)

7. A pack of no-slip socks so the outfit is complete from head to toe — especially at those indoor play places that make you take off your shoes. The grips on the bottom are key to keeping little ones upright as they explore.

Carter's

Price: $10 for four pairs (available in four color combinations)

8. A long-sleeved dress for the little one who refuses to wear anything that doesn't have a skirt. Maybe you can negotiate pants underneath if fun, flowy patterns are involved.

Carter's

Price: $10 (originally $24; available in six patterns and sizes 2T–5T)

9. A fleece pullover that might look somewhat similar to Mom's favorite go-to sweatshirt. Pick out matching colors for an adorable day of running errands with your mini me.

Carter's

Price: $14 (originally $28; available in three colors and in sizes 2T–5T)

10. A fleece vest outfit set for your toddler's next great outdoor adventure. Throw this on before you go hunt for leaves or forage for sticks on your favorite trail (or just your backyard).

Carter's

Price: $35 (originally $46; available in sizes 2T–5T)

11. A fleece dinosaur set if your little one is obsessed, but you're more of a ~neutral~ mom. The colors are muted, but the faux dino spiked hood will bring joy (and warmth in colder weather)!

Carter's

Price: $21 (originally $34; available in sizes 2T–5T)

12. A pair of trendy retro-inspired sneakers with faux laces and easy-to-buckle Velcro, so even a toddler in their "I can do it myself!" phase can get these on.

Carter's

Price: $19 (originally $38; available in sizes 4–12)

13. A waffle-knit shirt for an outer layer that will pull together any outfit for preschool, Grandma's house, holiday photos, or anywhere the day takes you.

Carter's

Price: $18 (originally $30; available in sizes 2T–5T)

14. A tulle skirt if your daughter is like mine and wants to wear a Tutu *everywhere.* This one is long enough to wear on its own so your little one can twirl, twirl, twirl while asking Alexa to play their favorite Frozen song again, and again, and again...

Carter's

Price: $22 (available in sizes 12M–6)

15. A cardigan that is a constant go-to in your toddler's closet for those in-between weather days when you need something cozy but not *too* warm.

Carter's

Price: $26 (available in two colors and in sizes 2T–5T)

16. A long-sleeve T-shirt for when you want a basic that doesn't have any of the typical characters, construction trucks, cars, and creatures.

Carter's

Price: $6 (originally $7; available in five patterns and in sizes 2T–5T)

17. A pair of ballet flats that will help your little one show off their fancy footwork at any upcoming holiday parties or other special events (even if it's just dress-up day at school).

Carter's

Price: $26 (originally $34; available in three colors and in sizes 4–12)

18. A festive two-piece set if you're the organized type who starts prepping for the holidays when the 'ber months hit. The tulle detail on the shirt might satisfy dress-obsessed toddlers, while the pants satisfy your need to keep them warm.

Carter's

Price: $26 (originally $34; available in sizes 2T–5T)

19. A Bluey sweatshirt, because maybe they'll just stop delaying getting dressed if their favorite TV friends can be with them all day long.

Carter's

Price: $17 (originally $34; available in two patterns and in sizes 2T–5T)

20. A hooded sweatshirt dress that will make you wish they made it in your size. For states that don't have true winters, this lets your toddler experience the coziness of a hoodie without overheating.

Carter's

Price: $24 (available in two colors and in sizes 12M–6)

21. A fleece set for those days you just want a monochromatic fit to take the guesswork out of getting your toddler dressed for the day.

Carter's

Price: $28 (available in three colors and in sizes 2T–5T)

22. A wildflower sweater because your little one doesn't stop growing in winter, so their wardrobe should keep blooming, too.

Carter's

Price: $24 (available in size 2T–5T)

23. A pair of wide-leg jeans with darling flower detailing that is small enough it's still easy to match with other patterns on top.

Carter's

Price: $23 (originally $38; available in sizes 2T–5T)

24. A pair of corduroy pants so your little one can match their favorite teddy bear while still vying for best dressed in their pre-school class.

Carter's

Pair it with the cute otter sweater! 

Price: $28 (available in two colors and in sizes 12M–6)

25. A denim button-down shirt that can be styled for whatever look you, I mean your toddler, wants to achieve. From city to country, or maybe a Yellowstone-inspired rancher costume for Halloween.

Carter's

Price: $20 (originally $32; available in sizes 2T–5T)

26. A pair of pull-on sneakers, because letting your toddler gain some independence doesn't have to be frustrating. These slip right on and with a little wiggling, you're out the door with a lot fewer tears!

Carter's

Price: $26 (originally $34; available in sizes 4–12)

27. A matching set that has more structure (and bows!) than their favorite PJs, but the same stretchy softness so your little one can play without constraining cuts or stiff fabrics.

Carter's

Price: $21 (originally $34; available in sizes 2T–5T)